4-Fluorobenzoyl chloride → N-(1-benzylpiperidin-4-yl)-4-fluorobenzamide

HRID 49773

Reaktionsgleichung

Reaktionsgleichung von HRID 49773
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>ClCCl.C(N(C(C)C)CC)(C)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][C:16]([F:15])=[CH:17][CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 678794-Fluorobenzoyl chlorideHCID 4158521-Benzyl-4-piperidylamine

Produkt 1

HCID 702501N-(1-benzylpiperidin-4-yl)-4-fluorobenzamideAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel3×HCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

To a solution of 1-benzyl-4-aminopiperidine (1.13 g) in dichloromethane (10 ml) were added a solution of 4-fluorobenzoyl chloride (0.99 g) in dichloromethane (1 ml) and diisopropylethylamine (1.09 ml) under cooling on an ice-water bath. The mixture was warmed to ambient temperature slowly under stirring. The mixture was diluted with dichloromethane and washed with water, saturated aqueous sodium hydrogen carbonate, water, and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. A residue was purified by column chromatography (silica gel 100 ml, dichloromethane:methanol=15:1). After rinse with diisopropyl ether-n-hexane (1:1), N-(1-benzylpiperidin-4-yl)-4-fluorobenzamide (1.31 g) was obtained.

Aufarbeitung

  1. temperatureunder cooling on an ice-water bath
  2. washwashed with water, saturated aqueous sodium hydrogen carbonate, water, and brine
  3. dry with materialAfter drying with magnesium sulfate
  4. customthe solvents were removed under reduced pressure
  5. customA residue was purified by column chromatography (silica gel 100 ml, dichloromethane:methanol=15:1)
  6. washAfter rinse with diisopropyl ether-n-hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2a6f47bbdaae4925b1a064929ab38b76
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710043B1

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